From Transportation Insurance to Lollapalooza: One Agent’s Incredible Journey

When James Chippendale stepped onto the field at Grant Park in Chicago last Thursday, he was cool and collected. It was the day before Lollapalooza, the 20-year running, three-day music festival that during its inception helped launch the careers of acts like Red Hot Chili Peppers, Pearl Jam and The Smashing Pumpkins. Dressed in a white t-shirt and jeans and wearing a black baseball cap and dark sunglasses, a passerby would likely mistake him for a touring band member, and not the insurance agent in charge of the entire festival.

“I’ve always been in hospitality ever since I was 15 years old, whether that be bartending in a restaurant or assistant managing a bar—even all the way down to doing dishes in the kitchen,” Chippendale says. “When I [finished college], I went to work for my father’s insurance brokerage firm. I’m actually third generation insurance, so I thought I’d give it a shot.”

His father’s firm specialized in transportation insurance, but when Chippendale started working at the Dallas office, he found it really just didn’t interest him. Without leaving his new job, he instead decided to take what he was interested in—the entertainment industry—and spin it into something that could work.

“I had a few friends in some nightclubs and bars, and I started writing their insurance and I liked it,” Chippendale says. “I went out and developed an entire marketing program to get to more bars and restaurants and nightclubs, and that’s how I really started, [by] focusing on that market segment.”

At the young age of 22, Chippendale built the entertainment segment up at his father’s firm on his own, bringing in about 100 new clients over the course of two years. When it had gotten to a point where his father was merely processing the paperwork, Chippendale approached him about branching out to start his own brokerage firm.

“He was very supportive,” he says. “I opened up a little shop—me and one assistant—and kind of just tried to find my way out there. I really focused on that business for years and years and years. At one point we had about 500 [employees] across the country.”

Young and constantly exposed to the VIP treatment, Chippendale had found his own personal passion within the insurance industry. And as he grew professionally, he began to see a need for insuring one-time special events.

“Some of the bars, nightclubs and live music venues that I was insuring would do these one-off events and I would have to go and find them coverage,” Chippendale says. “And I thought, ‘Wow, if these guys are doing it, there’s got to be thousands and tens of thousands of these around the country that are having problems getting these one-time special events.' It’s not easy—it’s a lot more complicated than you think.”

He found a niche in providing short-term special events coverage and started a division within his brokerage firm. With his career on the rise and his business full of promise, Chippendale suddenly fell ill with leukemia. Facing chemotherapy, radiation and ultimately a bone marrow transplant, he had a long battle with a very aggressive cancer ahead of him. Chippendale’s father was living in Texas at the time and stepped in, along with his assistant, to help run the business side of his firm and hold things together as best as possible in his absence.

“I did lose a lot of business while I was gone. I didn’t take one business call—not one business email—for two years,” he says. “I came back and the business was still there, but I had a life-changing experience.”

Chippendale was determined to do what he really loved from that point on. He brought on a partner and turned over the nightclub, bar and restaurant business to him so that he could devote his time and attention to special events coverage. He was writing somewhere between 10 to 20 events per month at that time, but knew he could take it to the next level.

Chippendale cites the 2003 fire at The Station nightclub in West Warwick, R.I.—one of the deadliest fires in American history that was caused by pyrotechnics during a Great White performance and ultimately killed 100 people—as an industry-changing event for the insurance world, but most especially for his business in special events coverage. All of a sudden, insurance came into focus with regard to large-scale events that had a lot of people gathered in one place.

“My business quadrupled overnight after the Rhode Island fires because everybody had to have proof of insurance,” he says. “It was like, ‘Wow. We really do need to make sure that everybody has insurance.'”

Diane Rusignola ( is IA managing editor.